Jacqueline Joins the Mile High Club!
by kendrickcamps
Summary: (Unbreakable Kimmy Schmidt) Jacqueline has the most anxiety-filled flight of her life. An unexpected fellow passenger makes her forget all of it. Rated M for future smut.


**_A/N:_** ** _So I started writing this in May of 2016 while sitting in between my sleeping parents on a flight from Atlanta to Denver. It's been my main priority and the reason why I haven't published anything since last January. There's a second chapter with smut coming, I promise. I just didn't want to make what I wanted to be a oneshot a super long novel._**

* * *

 **"The best things in life are unexpected because there were no expectations."br /**

 **― Eli Khamarov**

After her divorce from Julian, Jacqueline thought everything in her life had gone to shit. She was left with a measly twelve million, no home to call her own, and her son. Granted, she was happy to finally learn what it truly meant to be a mother, but her lack of Veras and Hunongs in her life was not making her situation any better. Her trophy wife status had been pulled right out from under her like the Savonnerie rug she pulled out from under Mimi Kanassis. She wasn't used to being a boring, rich husbandless person, but that wasn't going to stop her from trying to live as normal of her definition of a life as possible.

Jacqueline knew she deserved a break after the stress and emotional turmoil she went through during her divorce. She knew she deserved to get away from the East Coast, even if it was for a week. She knew she deserved the time to relax on a beach that didn't mostly contain condom wrappers and hobos, even if it was with her son.

"Come on, Buckley," Jacqueline attempted to coax the young boy behind her, who was completely mesmerized by his Nintendo DS, onto the plane. She had dealt with these kinds of families in her stewardess days and she refused to be known as "that lady" with "that kid".

"Buckley," Jacqueline repeated sternly, snapping her fingers in front of her son's face. Because of her lack of parenting experience, she had no idea whether she was being too stern or if she wasn't being stern enough. Either way, her attempted sternness had no effect on Buckley.

"Buckley, if you don't get on the plane and sit down, I will open the door mid-flight and throw you and that thing out of here."

Buckley immediately paused his game and looked up, wrinkling his nose. His mother had thrown his iPod with the 22-karat gold case out the window of their moving car because he wouldn't stop playing what was, in her opinion, the world's most annoying song in the history of adult contemporary music (You by Jim Brickman, of course). He did not want to test her limits.

"Move it, lady!" A deep voice dripping with a Brooklyn accent called from the line behind Jacqueline.

Jacqueline tugged Buckley by the backpack strap towards their seats, which were right next to the lavatories that separated business class (where they were) and first class (where she wished they were), before she had the chance to be attacked by an angry New Yorker.

"What's that guy's deal?" Buckley grumbled as he plopped down in his seat, keeping his eyes glued to his game.

Jacqueline scoffed and rolled her eyes in frustration. Times like these made her strongly regret neglecting her motherly duties while her children, mostly Buckley, grew up. It was one of the only instances where she wished she would have been her own Vera or Hunong instead of using actual Veras and Hunongs.

The plane was as peaceful and quiet as a barely loaded plane could be, which helped ease Jacqueline's onset of anxiety. She had experienced quite a bit of anxiety in her days of working for Haute Falutin Airlines, most of which was triggered by 9/11 and the various terrorist scares that she heard about, but she refused to tell anyone. Jacqueline White refused to be anything but normal. Well, her definition of normal (which was anything but).

"Where are they?" Jacqueline mumbled to herself, tapping her fingers rhythmically on the armrest of her seat as she eyed the line of people shuffling onto the plane. Before she had the chance to say or do anything else, a familiar, overly enthusiastic voice pierced her eardrums.

"This is just like what I've seen in my TV movies," Titus exclaimed as he stepped onto the plane, gripping his homemade fanny pack in one hand and his thrifted, two sizes too small Madonna sweatshirt in the other. "Except it's bigger. And Matt Damon isn't here."

Kimmy gasped loudly as she followed behind him. Her eyes widened like a little kid in Dylan's Candy Bar.

"This is incredible!"

Kimmy had never been on a plane this big before, mostly because no commercial airlines flew in or out of Durnsville Municipal. The plane she flew on to New York as a recently freed Mole Woman was a dinky little twin-engine plane, which was almost nonexistent in comparison to the Airbus she had just boarded.

"Come sit down next to Mama Titus," Titus called out to Kimmy, patting the cushioned seat next to him and dropping his carry-on items at his feet.

Jacqueline sighed and rolled her eyes as Kimmy skipped enthusiastically from the entrance to her seat, which was a solid six feet. Initially, she was excited that Kimmy was tagging along so she could spend some quality, personal time with her, but that slowly faded as her plans turned from vacation to field trip. It was most likely the anxiety causing her to be unusually irritable, but she wasn't going to survive the flight if Kimmy was going to continue with her inherent giddiness.

Part of Jacqueline was glad Kimmy and Titus could tag along, seeing that she had never been to the West Coast and traveling with two other people who had never been to the West Coast seemed like it would be less stressful for her. Part of her wished Lillian wouldn't have been on her mandatory drug and alcohol rehab retreat and that Kimmy's overwhelming amount of pep and Titus's sass weren't tagging along on her well needed and deserved break from the city life and newly divorced life. In the end, though, her whole was moderately content with the fact that she had enough to distract her from her mess of a life.

Jacqueline fidgeted as she watched the remaining passengers board the plane, some making their way past her and down the aisle of business class and others disappearing behind the first class curtains. The desire to move behind the powerful navy blue fabric caused a dull ache to resonate in her chest. She felt deep in her soul that she belonged with all the people up in first class, but her wallet begged to differ.

"Welcome aboard United Airlines flight 665 to Los Angeles, y'all!" one of the flight attendants announced cheerfully over the intercom in a thick southern accent. "We'll be takin' off here in about ten minutes, so make sure y'all have your personal items under the seat in front of you and carry-on baggage in the compartment right there above your head."

Jacqueline rolled her eyes as she listened to the thick accent of the flight attendant over the intercom. It wasn't the accent that annoyed her as much as it was the internal conflict of whether she was supposed to be a high-class trophy wife or a regular girl from an Indian reservation in South Dakota. Part of her wanted to believe she was destined to be the beautiful, stay at home trophy wife behind a man who paid for someone to wipe his ass, but the flight attendant's accent and her presumably down-home roots made Jacqueline second guess everything about that life.

"How much longer until we leave?" Buckley asked his mother, who was drumming her fingers impatiently on the armrest that separated her and her son as the flight attendant continued to brief the passengers with the standard safety procedures. "I want to see how long I can follow the plane with the drone dad got me for my birthday." Under any other circumstance, Jacqueline would immediately question why Buckley would do something so foolish and illegal, but she was far too distracted by her anxiety and internal conflict to care.

"Once again, I wanna thank y'all for choosing United Airlines. Hope y'all enjoy your six-hour flight to Los Angeles, California!" How the flight attendant was that cheery about being in a flying metal tube for more than two hours, Jacqueline had no idea. She was grateful, though, that she had finally stopped droning on about life jackets and imminent death in her annoyingly sweet Southern drawl.

To try to calm herself down and distract herself from questioning her whole entire life, Jacqueline observed from a short distance as Kimmy and Titus took turns playing with the window shade. As much as she attempted to force furrowed brows to accommodate her mood, a subtle grin creeped across Jacqueline's lipstick-tinted lips as she listened to Kimmy go on about how cool and fascinating the window shades were and Titus immediately reply with a "It sure is, Kim Tebow!" and childlike giggles. She wanted so much to be annoyed by the two _clearly_ uncultured, middle-aged adults, but she couldn't help feel a warm, motherly feeling inside. It was almost like watching two of her very own crotchfruits discover the luxurious wonder of the airplane window shade.

Jacqueline continued watching her two companions explore the different parts their area of the cabin in awe until she felt the jet engines fire from either side of the plane. She felt all the color drain from her face as the seatbelt sign lit up right in front of her. Jacqueline's anxiety, temporarily overshadowed by the glee Kimmy and Titus's joy caused her, began emerging once more. She immediately began talking herself down in her mind.

 _You're going to be fine. The plane is going to be fine. The flight is going to be fine. Nothing fatal is going to happen. You're freaking out for no reason._

Jacqueline's tapping on the armrests she sat between began to increase pace. She may not have been verbalizing her thoughts, but her facial expressions could've made anyone think otherwise.

 _You will survive the flight that you paid $400 for. You have a bottle and a half of Xanax in Buckley's backpack. You're going to be fine._

"Ms. White?"

Jacqueline squeaked as she felt a permanently calloused hand rest itself on her forearm. She sighed, relieved as she looked over and saw Kimmy leaning across the aisle towards her.

"Are you alright?"

"Yes, of course!" Jacqueline immediately replied with forced enthusiasm. She wasn't going to break down, especially in front of the evidently unbreakable Kimmy Schmidt. "Why would you ask such a thing?"

"Well," Kimmy began, motioning to Jacqueline's cheeks, "you look as white as Gretchen was when she watched Lil' Lisa walk out of the bunker and into what she thought was a never-ending lake of fire and all that bad stuff Reverend Richard told us about."

Jacqueline was completely conscious of the fact that all color in her face was disappearing due to her raging anxiety, but she patted her cheeks to give Kimmy, who was anything but dumb, the impression that she was unaware that she was in the midst of a meltdown.

"Oh my, really? I had no idea!" Jacqueline exclaimed, rubbing the fleshiest part of her cheeks in attempts to draw some of her natural pinkish tint back. "That skin therapy where they hang you by your feet and rub mayonnaise on your face with industrial sponges must be working!"

Kimmy shot Jacqueline a knowing glare and patted her forearm. The signs of anxiety and panic were all too familiar to her and she didn't want Jacqueline to feel obligated to conceal it.

"You're also shaking like one of those little toys... what are they called?" Kimmy tapped on Jacqueline's forearm with her index finger as she racked her brain trying to remember the name of one of her favorite toys she owned before she was kidnapped and held hostage in the bunker for well over a decade.

"A Shiatsu wand vibrator?" Jacqueline questioned only loud enough for only Kimmy to hear, immediately eliciting a scrunched-up cringe face from Kimmy. The only toys she'd ever had experience with were in the form of an iPad, dolls made from corn husks, and sex toys. It wasn't Jacqueline's fault that the only vibrating toys she had ever dealt with were the ones that were sold at adult stores.

"No!" Kimmy exclaimed in a hushed tone and shook her head, trying to rid her mind of the very thought of her friend-boss with a vibrator of any kind. She couldn't bear to look at Jacqueline like that, even if she may have secretly wanted to. "I think it was called a Bumble Ball."

"Oh," Jacqueline responded, looking down at her hands and trying to brush off the fact that she had just mentioned one of the various toys she owned and possibly brought along with her on the trip. Before Kimmy had acknowledged it, she hadn't noticed how much she was _actually_ shaking; it was something she did a lot and tended not to focus too much on. "I'm okay, Kimmy, don't worry." Jacqueline attempted to assure Kimmy that her anxiety wasn't as bad as it appeared to be (and was) by patting the top of Kimmy's hand, which was still on her forearm.

Kimmy's knowing glare returned. Instead of continuing with her attempts to get Jacqueline to talk about her feelings, she retracted her hand and leaned back over towards her seat and Titus, who was fast asleep against the closed window shade.

Jacqueline let out a sigh and peered over at her son, who was still completely engrossed in his video game. If Buckley was okay and completely unfazed by the fact that they were about to be in a flying death trap for six hours, Jacqueline figured she could be as well. She let out another sigh and let her eyes fall closed, focusing on her shallow breathing until she fell asleep.

About an hour of the flight passed while Jacqueline slept. Buckley played various games on his Nintendo DS, stopping only once to tell one of the flight attendants that he wanted a Coke on the rocks and that his mother would pay for it. Kimmy sat in silent wonder, peering around at the flight attendants and the passengers and mentally comparing what she had seen in Titus's TV movies and what was happening around her. Titus, much like before Jacqueline had fallen asleep, was snuggled up against the window shade, using his Madonna sweatshirt as a pillow.

Jacqueline's dreams were anything but normal when she dealt with her anxiety. They ranged from ridiculously sexual to ridiculously violent, which was only a step up from Jacqueline's usual dreams, but they were unusual nonetheless. The dream she was having during the first part of the flight, though, was a mix of both, resulting in her unconscious body becoming what she often referred to as "a projection of my brain on heroin".

The muscles in Jacqueline's thighs visibly tightened through the incredibly tight skinny jeans she donned. She white-knuckled the edge of both of her armrests and began breathing shallowly once more. Muscles throughout her body contracted as she writhed in her seat. She drowsily mumbled what sounded like gibberish or possibly a Satanic chant. Anyone who watched her probably thought she was crazy, but only she and her friend-nanny knew what was occurring was anything but unusual.

"Is she okay?" the flight attendant with the snack cart, a stout woman who appeared to be in her early 50s, directed her question towards Kimmy, who was attentively watching Jacqueline from across the aisle. "She looks like she's having a seizure." The woman looked on as Jacqueline continued writhing, a look of concern displayed on her face.

After a few more moments of observing Jacqueline, Kimmy diverted her gaze from Jacqueline to the flight attendant.

"She's alright!" Kimmy began, moving her balled up fist from under her chin, "She's just dream projecting."

"Okay then," the flight attendant responded, looking back down at Kimmy. "Well if you're able, can you get her to stop? She's scaring a family a few rows behind y'all." The flight attendant peered over her shoulder at a family of three, who were all staring at Jacqueline's erratic sleep movements with looks of confusion and fear on their faces.

Kimmy grinned and nodded at the woman, watching her push her cart full of goodies past the business class lavatories and through the blue curtain to begin serving those with more money than Kimmy could ever imagine having.

Minutes passed as Kimmy returned her attention to Jacqueline, whose dream projections had mellowed out significantly since the kind flight attendant informed Kimmy that she was scaring people. Her breathing had returned to normal, as had her muscle movements and grip on the armrests. She stopped subconsciously summoning the devil, but started repeatedly (and rapidly) mumbling something along the lines of "Deirdre" or "dungeon". Kimmy wanted to ask, but was afraid to know what exactly she was going on in Jacqueline's mind.

"Attention passengers," a deep voice called over the intercom, waking Jacqueline from her now very light anxiety sleep. "We're about to head through some turbulence, so I ask that you please stay seated and keep your seat belts fastened." Immediately, the cabin began trembling like Jacqueline's hands, eliciting moans and groans out of the many passengers.

"Holy…" Jacqueline rubbed her eyes, sitting up in her seat and surveying her surroundings. The last thing she remembered, Kimmy was judging her from across the aisle with what she could only describe as a judgmental badger face. Jacqueline peered over at Kimmy who was, in fact, still looking at her. Instead of squinted eyes and a scrunched face, though, Kimmy looked on at her boss-friend with much more caring eyes than before.

"Well good morning to you, Ms. White." Kimmy flashed a cheesy grin at an extremely disoriented Jacqueline as she moved her fist from under her chin to her armrest. "Did you sleep well?"

Jacqueline opened her mouth to answer, but caught a glimpse of the family she had startled in her peripheral. They continued to stare at her as if she was some zoo animal or a half-naked girl who danced in a cage at the bar she frequented when she first moved to New York. Her mood shifted from dazed and confused to annoyed and embarrassed, causing her body to tense up once more.

"Did I dream project?" Jacqueline grew incredibly self-conscious, sitting up in her seat and straightening herself out as if to erase what had just occurred from any onlookers' minds. She had dream projected a countless amount of times, but unlike this time, they were all in the privacy of her own home, where only Kimmy or occasionally Vera saw her. Her heart pounded loudly in her ears as she continued to watch the gawking family out of the corner of her eye.

"You kept saying either 'dungeon' or 'Deirdre'," Kimmy replied with a slow, hesitant nod, a look of confusion displayed on her adolescent-looking face.

"Oh, dear God," Jacqueline immediately replied in a worried tone, straightening herself out even more and redirecting her attention to the blue curtain in front of her to distract herself. The anxiety she had just slept off was quickly returning and Jacqueline wasn't sure how much of it she could handle.

"What happened in your dream, Ms. White?" Kimmy questioned as she sat back in her seat, trying to figure out what a dungeon and Deirdre Robespierre had to do with each other.

"Don't worry about it," Jacqueline immediately snapped back. She wasn't about to explain to Kimmy, in front of God and everyone within earshot, why her subconscious decided to put her in something of a sex dungeon with her arch nemesis.

As the turbulence settled and the seatbelt light was turned off, Jacqueline mustered up enough courage and energy to excuse herself to the lavatory that was only five steps, at the most, away from her seat. She wasn't going to spend the remainder of the flight being silently criticized by the Judgey McJudgersons and anyone else who may have seen her dream projections. Even if they weren't saying anything (anymore), Jacqueline could feel it and she was _not_ enjoying it.

"Kimmy," Jacqueline began as she approached the door, turning around to eye her son, who was flipping through a very graphic Japanese adult magazine that he had received from a middle-aged first class passenger using the lavatory during her nap, "watch… _that_." She rolled her eyes and scoffed as images of her ex-husband doing the same thing on the flight home from George Bush's second inauguration came to mind.

Kimmy looked up from the Family Circus comics she had been given by the young girl that sat behind her and smiled.

"Will do, boss!" Kimmy responded cheerfully, clicking her tongue at an extremely distracted Buckley only to have him respond with "Shut up, I'm looking at New Age boobies."

Jacqueline sighed as she swung the door open and walked inside the small airplane bathroom. She closed the door behind her and locked it, checking a couple times to make sure it was, in fact, locked. After a few incidents working on Julian's net jet flights, she was extra careful to make sure the door was secure enough to remain closed during turbulence or someone attempting to _actually_ use the bathroom.

Jacqueline's anxiety began consuming her again, causing her to shake like a Shiatsu wand vibrator and hyperventilate like she only had half a lung. She moved a couple steps to stand in front of the large, but extremely dirty mirror and attempted to evaluate whatever the hell was going on.

"What is wrong with you?" Jacqueline audibly questioned herself, shame clearly displayed in her voice. "You're a grown ass woman and you're acting _worse_ your 10-year old son. Grow the hell up, Jackie!" She pounded her fists on the plastic lavatory sink in frustration as tears began to well up in her eyes. Repressing her feelings and personal "issues" (though she would never admit to them being _actual_ issues) had done Jacqueline so well for so long. She had rarely questioned her lifestyle or her decisions. What made her suddenly second guess everything? What was so different now?

As Jacqueline stood at the sink and thought about how much she didn't understand her own life, a loud knock resonated from the other side of the door. Jacqueline looked up from the dripping sink faucet with dried tears on her cheeks and redirected her attention to the door.

"Uh, j-just a minute!" Jacqueline called out to the stranger on the other side of the door as she wiped the smeared makeup from under her eyes to make herself seem as calm and put together as possible.

As Jacqueline dug at the mascara that had tear stained the skin right under the corner of her right eye, another knock came from the other side of the door. Annoyed, Jacqueline quickly discarded the used balls of toilet paper into the toilet behind her and flushed with her foot. She learned in her days as a flight attendant that you were more likely to get herpes from an airplane bathroom than an actual human being.

"Must you be so impatient?" Jacqueline berated the rude passenger as she opened the lavatory door. "What if I –" Before she could propose the possibility of her having explosive diarrhea, she was shoved back into the lavatory by the hooded individual and a pair of unusually familiar hands.

"What the hell?" Jacqueline exclaimed, standing a few inches in front of the toilet. She watched in anger and confusion as the person who forced her back into the bathroom slammed the flimsy door shut and fiddled with the lock. Jacqueline wanted to scream at this inconsiderate and incredibly invasive person for forcing her back into the germ-infested hell hole, but she was speechless. Instead, she stood with her mouth agape as she watched whoever was under the hood continue to struggle with the lock.

"Are you drunk or incredibly stupid?" Jacqueline finally managed to ask, reaching for the lock.

"No," the female passenger began, successfully locking the door and grabbing Jacqueline's hand, "just drunk. We both know my IQ is approximately a hundred points higher than yours." She turned around and flashed a toothy grin at Jacqueline.


End file.
